94-26-8 Usage
Description
Butylparaben is an antimicrobial agent used in pharmaceutical suspensions, characterized by its ability to inhibit the synthesis of DNA, RNA, and enzymes such as ATPase and phosphotransferase. It is commonly used in combination with other parabens, primarily methylparaben and/or propylparaben, in various medications and is found in numerous over-the-counter (OTC) products, including Tylenol, Drixoral, Maalox, and Mylanta.
Uses
Used in Pharmaceutical Industry:
Butylparaben is used as a preservative in pharmaceutical formulations for its antimicrobial properties, particularly against molds, yeasts, and to a lesser extent, bacteria. It helps maintain the stability and safety of medications by retarding microbial growth.
Used in Cosmetics Industry:
Butylparaben is used as a preservative in various cosmetics, including creams, lotions, ointments, and other skincare products. Its ability to inhibit the growth of molds, fungi, and yeasts contributes to the shelf life and safety of these products.
Used in Food Industry:
Butylparaben is used as a preservative in a wide range of food products such as salad dressings, mayonnaise, spiced sauces, mustard, frozen dairy products, and baked goods. It helps to prevent spoilage and maintain the quality of these foods by inhibiting the growth of undesirable microorganisms.
Used in Dental Care Products:
Butylparaben is used as a preservative in dentifrices, ensuring the stability and safety of these oral care products by preventing the growth of harmful microorganisms.
Used in Commercial Solutions:
Butylparaben is added to solutions like commercially prepared low-ionic strength saline (LISS) solutions and beer to retard microbial growth, thereby extending their shelf life and maintaining their quality. In comparison to other parabens, butylparaben is considered the best antifungal agent, making it a preferred choice for these applications.
Production method
Butylparaben is derived from the esterification between p-hydroxybenzoic acid and butanol. Butanol and p-hydroxybenzoic acid are heated together for being dissolved, slowly added dropwise of sulfuric acid, continue the refluxing for 8h. After cooling, add 4% sodium carbonate solution, separate the water layer, steam out the butanol, let it cool, filter to obtain the crude product, and then carry out ethanol recrystallization (solubility in ethanol: 200g/100ml).Take sulfuric acid as a catalyst; derive it from the reaction between p-hydroxybenzoic acid and butanol.
Toxicity
ADI is subject to postponed decision (FAO/WHO, 2001).
LD50: 16.0 g/kg (mouse, subcutaneous injection).
Mice subjecting to short-term toxicity test have gotten inhibited weight increase. There have been reports regarding to the acute dermatitis for human beings. In the p-hydroxybenzoic acid esters, this product gives the best anti-corrosion effect, but also the largest toxicity.
Content analysis
2g (accurate to 0.1mg) was taken and dried in silica gel for 5h before being transferred to the flask. Add 40 mL of 1mol/L of sodium hydroxide, flush flasks with water. Cover the surface of the dish and apply a small fire to boil 1h before cooling. Add 5 drops of bromothymol blue solution (TS-56), titrate the excess sodium hydroxide with 1 mol/L sulfuric acid, and make the color of the solution consistent with the buffer containing the same indicator (pH 6.5). Carry out a blank test at the same time and make the necessary calibration. 1ml/L sodium hydroxide per milliliter corresponds to the 194.2 mg of this product (C11H14O3).
Usage limit
Japan (1998, calculated on p-hydroxybenzoic acid; the data in parentheses is the amount converted into equivalent amount of this product, g/ kg), soy sauce 0.25 g/L (0.35 g/L), vinegar 0.1 g/L (0.14 g/L); Soft drinks and syrup: 0.1 (0.14); fruit sauce: 0.2 (0.28); fruits and vegetables 0.012 (0.016).
Hazards & Safety Information
Category :Toxic substances
Toxic classification: poisoning
Acute toxicity:? Oral-mouse LD50: 13200 mg/kg; celiac-mouse LD50: 230 mg/kg
Stimulation Data:? Skin-Guinea Pig 5%/48 hours Mild
Flammability and Hazardous characteristics:? Thermal decomposition; pungent irritation Smoke
Storage and transportation characteristics:? Treasury: ventilated, low temperature and dry
Fire extinguishing agent:? water, dry powder, foam, carbon dioxide
Preparation
Butyl paraben is prepared by esterifying p-hydroxybenzoic acid with butyl alcohol in the presence of an acid catalyst, such
as sulfuric acid, and an excess of the specific alcohol.
Production Methods
Butylparaben is prepared by esterification of p-hydroxybenzoic acid
with n-butanol.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
Butylparaben is incompatible with strong oxidizing agents and strong caustics.
Fire Hazard
Flash point data for Butylparaben are not available; however, Butylparaben is probably combustible.
Pharmaceutical Applications
Butylparaben is widely used as an antimicrobial preservative in
cosmetics and pharmaceutical formulations.
It may be used either alone or in combination with other paraben
esters or with other antimicrobial agents. In cosmetics, it is the
fourth most frequently used preservative.
As a group, the parabens are effective over a wide pH range and
have a broad spectrum of antimicrobial activity, although they are
most effective against yeasts and molds.
Owing to the poor solubility of the parabens, paraben salts,
particularly the sodium salt, are frequently used in formulations.
However, this may raise the pH of poorly buffered formulations.
See Methylparaben for further information.
Safety
Butylparaben and other parabens are widely used as antimicrobial
preservatives in cosmetics and oral and topical pharmaceutical
formulations.
Systemically, no adverse reactions to parabens have been
reported, although they have been associated with hypersensitivity
reactions generally appearing as contact dematitis. Immediate
reactions with urticaria and bronchospasm have occurred rarely.
See Methylparaben for further information.
LD50 (mouse, IP): 0.23 g/kg
LD50 (mouse, oral): 13.2 g/kg
storage
Aqueous butylparaben solutions at pH 3–6 can be sterilized by
autoclaving, without decomposition. At pH 3–6, aqueous
solutions are stable (less than 10% decomposition) for up to about
4 years at room temperature, while solutions at pH 8 or above are
subject to rapid hydrolysis (10% or more after about 60 days at
room temperature).
Incompatibilities
The antimicrobial activity of butylparaben is considerably reduced
in the presence of nonionic surfactants as a result of micellization.
Absorption of butylparaben by plastics has not been reported but
appears probable given the behavior of other parabens. Some
pigments, e.g. ultramarine blue and yellow iron oxide, absorb
butylparaben and thus reduce its preservative properties.
Butylparaben is discolored in the presence of iron and is subject
to hydrolysis by weak alkalis and strong acids.
Regulatory Status
Butylparaben is regulated by the U.S. Environmental Protection Agency (EPA) under the Toxic Substances Control Act (TSCA) and the Federal Insecticide, Fungicide, and Rodenticide Act (FIFRA). In 1998 its pesticide registration status was listed as "cancelled" (U.S. EPA, 2003).Included in the FDA Inactive Ingredients Database (injections; oral capsules, solutions, suspensions, syrups and tablets; rectal, and topical preparations). Included in nonparenteral medicines licensed in the UK. Included in the Canadian List of Acceptable Nonmedicinal Ingredients.
Check Digit Verification of cas no
The CAS Registry Mumber 94-26-8 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 4 respectively; the second part has 2 digits, 2 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 94-26:
(4*9)+(3*4)+(2*2)+(1*6)=58
58 % 10 = 8
So 94-26-8 is a valid CAS Registry Number.
InChI:InChI=1/C11H14O3/c1-2-3-4-8-7-9(12)5-6-10(8)11(13)14/h5-7,12H,2-4H2,1H3,(H,13,14)
94-26-8Relevant articles and documents
A novel way to prepare n-butylparaben under microwave irradiation
Liao, Xiangjun,Raghavan,Yaylayan
, p. 45 - 48 (2002)
The synthesis of n-butylparaben under microwave irradiation in the presence of an inorganic salt ZnCl2 as a catalyst is reported. Using this specific catalyst for the synthesis of the n-butylparaben under microwave irradiation, not only shortens the reaction time, but also reduces the pollution from the use of concentrated sulfuric acid and prevents the complicated after-treatment handling problems. The reason for this type of microwave-assisted reaction is also demonstrated from the temperature profiles of the reaction. The ratio of the reactants for the better microwave energy efficiency is discussed. The use of microwave irradiation for the large-scale production of this type of food preservative is therefore feasible.
A recyclable cucurbit[6]uril-supported silicotungstic acid catalyst used in the esterification reaction
Xia, Wen,Nie, Yu-Mei,Lei, Na,Tao, Zhu,Zhu, Qiang-Jiang,Zhang, Yun-Qian
, (2021/05/05)
The esterification reaction used to prepare butyl paraben (BP) and propyl gallate (PG) catalyzed using a cucurbit[6]uril-supported Keggin-type silicotungstic acid (Q[6]-STA) catalyst has been investigated. The Q[6]-STA catalyst has been characterized using FTIR spectroscopy, XRD, SEM, EDS, thermal analysis, and surface area studies. Q[6]-STA was easy to prepare in high yield and exhibited some advantageous properties, such as high catalytic activity and its convenient recovery. Moreover, a reusability study showed that the Q[6]-STA catalyst was stable and active.
Proline ionic liquid and method for catalyzing synthesis of paraben by proline ionic liquid
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Paragraph 0059-0062, (2020/09/16)
The invention discloses proline ionic liquid and a method for catalyzing synthesis of paraben by the proline ionic liquid. The preparation method comprises the following steps: adding N-butylbenzimidazole, a solvent and proline into a dry three-neck flask, carrying out reflux reaction until the reaction is complete (monitored by TLC), evaporating to remove the solvent to obtain a faint yellow oilyliquid, namely the proline ionic liquid, adding p-hydroxybenzoic acid, alcohol and a proline ionic liquid into a dry three-necked bottle, heating to reflux reaction, monitoring by TLC until the reaction is finished, evaporating under reduced pressure to remove the solvent, extracting residues with diethyl ether, evaporating the diethyl ether phase to remove the solvent to obtain the methylparabenwith the yield of 88% or above, wherein the remainder is the ionic liquid, and carrying out washing and drying so that the product can be recycled for many times. The method disclosed by the invention is efficient, environment-friendly and safe, the catalyst can be recycled, the cost is reduced, the requirement on equipment is low, and the method is an efficient method for synthesizing paraben.